Who are you?

I’m Matthew Valentines.  Online dating coach, concierge, and founder of Personal Dating Assistants.  I help single guys get dates with attractive women online.  Hitch?  It was a cute movie.  Welcome my reality.

As an online matchmaker, I believe in treating the men I do business with like family, and the women in my life with respect.

Being a digital nomad, with a rapidly growing business, I live a pretty cool life. But it wasn’t always this way.


How’d you get into the online dating game?

I was into technology and building businesses early.  I think it was 1994, when we got disks in the mail for a new service called “America Online”.  I remember installing it, firing up my modem, and finding my way to the “singles” chat room.  Before I knew it I was messaging with a cute local girl, and we met up for ice cream.  After that first experience as a 15 year old, I was convinced that online dating was the coolest thing ever.  I still feel that way.

Of course, that was just dumb luck.  It would take me many years before understanding all the subtleties of online dating.  Much less master it.  Even after college, I’d only been with a few women.

Then once again as luck would have it, my sweetheart became my fiancee.  We lived together for 5 years, during which I put my dating life on hold.  That is, until the day she left me for a wealthy, older man.


Going through that breakup left me devastated.  I experienced a massive dose of insecurity and uncertainty, since she left me for what I perceived at the time to be a higher value guy.

But I think the main reason it hurt so bad, was because I was convinced I’d never meet another girl as good as her.  To make sure I’d never feel that way again, I vowed to crack the online dating code, so I would always have options.  But there was 1 problem: I didn’t have a clue about how to strike up a conversation with a new girl in person.  Much less keep it going.

So I hit the pause on dating online, recognizing that I needed to first develop solid in-person skills to support it.

What was your experience like?

I could not approach at first. I’d stand there, my back against the wall, unable to move from approach anxiety. Eventually I was able to open my mouth to speak, and create a conversation from nothing. From there, I held conversations longer and longer, until about 3 months in, I finally saw some results.

After that, I was making it happen on a regular basis. During those early years, I definitely had my fill of the bar & club scene. I’m glad I got the experience under my belt, but it got old, and it didn’t make me happy. I was tired of meeting party girls. I wanted better quality.  And a better way.  So I dove head first into day game.


Daygame was exponentially more difficult at first, but I was eventually able to approach at the mall, parks, and universities like second nature. I’d ask for directions, make small talk, suggest an insta-date, escalate, and eventually make it happen. This was great stuff when I was in my 20’s, with plenty of time on my hands, and the stamina to holler all day, until I’d meet a woman who was hot to trot.

Eventually, I was able to transition my dating success into a business, as a dating coach for men.  Helping other guys get this area of their life handled was rewarding.

How did you become an online dating expert?

As I got older, I found myself with less time, and more responsibilities. I could no longer justify the focused time & energy day game required, much less the nightlife scene.  I had to find an even more convenient method, if I was to continue meeting women consistently.

Mind you, I had always supplemented my in-person effort with online dating.  But the environment was still in a relative infancy.  AOL chat rooms and Yahoo Personals were being shunned in favor of Craigslist & Myspace.  Match.com was growing.  The online dating scene slowly became more mainstream.  The quality of women logging on started going up…along the level of competition to get their attention.


Like a mad scientist, I experimented with everything during those years, and kept detailed spread sheets.  I would create profiles of pretty girls, just to stay on top of what guys were saying.  If anything struck me as funny or useful, I’d assimilate it.  Like the Borg.  If I haven’t geeked out enough for you yet, like Neo in The Matrix, I started recognizing patterns.

After 20 years on the sites, I developed a 6th sense for what to say, when to say it, and who I was saying it to.  With a skill set that allowed me to line up multiple dates with attractive women each week, I had a paradigm shift away from in-person approaches, and focused on online almost exclusively.  The quality of women I was dating from online got better & better,  By the time I had to start using Excel just to keep track of all their names, I said goodbye to the bar & club scene for good.

I perfected my online dating system.


Why a dating consultant?

I love the online dating game. But it’s exhausting.  As men, we have to do everything.  Grab her attention, create a conversation, make her laugh, convince her you’re not a serial killer, suggest a get together, overcome objections, and get rejected multiple times before winning that 1 coveted baby step token of pre-approval…her phone number.

I was at the point in my life professionally where it didn’t make sense anymore to be doing the hard work myself.  The only problem was, I couldn’t find a dating assistant competent enough to outsource my online dating life to.  I tried everything, from Craigslist, to Task Rabbit, to a number of other virtual assistant companies with a promising pitch, but ultimately disappointing results.

I knew the whole thing could be done better.  But if I was going to teach someone to do it for me, then I was going to have to teach them myself.  Using my own system, which took me 20 years to perfect.

Why did you start Personal Dating Assistants?

The 4 Hour Work Week by Tim Ferriss was the inspiration behind the business concept.  He’s definitely one of my heroes.  Reading about how he lifehacked his way to success, by outsourcing his repetitive tasks to virtual assistants.  I knew it was a natural fit for guys looking for more dating opportunities online.

But while the up-front pre-qualification phase of online dating is systemizable & repeatable, anything that comes after that point is way more personal.  I didn’t want my dating concierge to play “getting to you know you” with women on my behalf.  I simply want my dating assistant to make the introduction, suggest a get together, and exchange contact info, so we can see if we have chemistry in person, or not.

Recognizing that I probably wasn’t the only guy who would like the concept, I trained people as an online dating coach, and we grew it into the Personal Dating Assistants company organically.  The rest is history!

The goal was do things differently from the traditional professional matchmaking services.  As a result, we get lots more dates for our members.  Often with some of the most desired women on popular sites like okcupid, match.com, and tinder.


What’s it like to be an online dating coach?

Last year I ditched my high rise, and went 100% location independent.  I live out of just 2 suitcases these days. Literally no permanent address.  The travel freedom it brings is unbelievable.  Most of the teamwork we do at Personal Dating Assistants is virtual, but we still maintain a small office presence in the online dating capital of the world, New York City.

What role do women play in your life right now?

I have 1 wonderful woman in my life right now. We met of course, online. But back in the day, I might have had 3 to 4 open relationships going at any given time. Any more than that, is just impossible to manage. Most guys don’t realize, but after you crack the online dating code, meeting women is the easy part…keeping them happy after a few months is the hard part!  Women ultimately want a serious relationship, and if that’s not in the cards, she’s eventually gonna move on to find a more commitment oriented guy. It’s not a question of if. It’s a question of when.

From my perspective, even the most successful single men would love to meet the right woman.  But until they do, they see nothing wrong with spending quality time with miss right now. Most women have this same attitude about men, but rarely admit it outside of their close girlfriends. The meteoric rise of Tinder reflects that.


Any parting words of wisdom?

I want guys to know that wherever they’re at in their personal journey, they don’t have to do everything themselves. My big “aha” moment came when I realized that rather than try to do everything alone, it can make more sense to outsource your online dating, and trust the expertise of others. Not every man is at that point in his life to use an online matchmaker.  But for those who are, it’s worth pondering if it still makes sense for them to be doing all the hard work themselves.